TwentySomething: Regret Minimization

Karthik Senthil
3 min readDec 2, 2015

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If you didn’t read the first TwentySomething episode about the Heliotropic Effect, please check it out! Enjoy Episode #2 and stay tuned for the next one!

Recently, I decided to leave my job to take some time off and figure out what I wanted to do next. It wasn’t an easy decision — in fact, it was kind of scary. But, why was it scary? It’s not like I had any semblance of hardship awaiting me (I’m extremely fortunate to have a safety net of supportive family, friends, and some savings from prior jobs). I spent some time thinking about it and expected the answer would be a sensible and intelligent one. It turned out that it was actually much more myopic than I had hoped: I was simply afraid to fall behind.

I wasn’t comfortable grappling with the fact that while my peers were seemingly moving ahead career-wise and financially, I was idling by. I knew that this stagnancy wouldn’t last forever, but in the moment, I instinctually couldn’t bear choosing this over moving in some direction, any direction. Now, a few weeks removed and looking back, it seems irrational and even a bit vain. How could I let something so meaningless affect this important life decision? I believe my experience is emblematic of and speaks towards the broader human condition: life’s inertia makes us innately resistant to change. As a result, we tend to optimize around our immediate, short-term interests (i.e. “just keep the train moving”) above all else, even if there are objectively better options.

When Jeff Bezos — now founder and CEO of Amazon.com — was deciding whether or not to leave his stable, well-paying job to go start a company selling books online, he used what he terms a regret minimization framework to help him make this decision. What this means is he asked the future 80 year old Jeff Bezos which he would regret most and chose the answer where future regret would be minimized. He concluded that while he may regret leaving his job, he would always regret not trying to start this company.

I think this framework offers a fascinating methodology on how to combat our inertia by filtering out short-term “noise”. I know my 80 year old self would far more regret not taking time to figure out what I really want to do next over any short-term discomfort. And I’ll bet that your 80 year old self will far more regret not taking a chance to challenge yourself on something that’s interesting, difficult or just plain wacky over missing out on any financial or social stability. This shouldn’t be the only perspective you use when facing decisions, but its a healthy one to engage in. Look — ultimately, life’s destination is the same for all of us, so why not make the most out of the journey?

If you enjoyed this, please click the heart button so more people see this! If you have any comments about what you’re not liking, please post them here or just email me at karthik.senthil@gmail.com. Like I mentioned, I’ll probably be doing ~10 of these over the next few weeks in different styles + formats, so keep reading and as always, appreciate all the ❤ and support!

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